2 Answers
2

The normal way to verify data deletion would be to treat the device as block storage and read all the data off and verify that no sensitive data remains. Apple doesn't allow this kind of access in normal iOS operation, so your friend will have to wipe the iPad using Settings, and then jailbreak the device, which will allow installation of tools (e.g. SSH) to access the raw data blocks on the iPad.

This is laborious and probably a waste of time. Recent iOS devices, including iPad 2, use full disk encryption for data on the device. To wipe the data on the device, iOS overwrites the encryption keys, reasoning that without the encryption keys the data cannot be recovered. I've read of data being extracted from iOS devices, but never after the encryption keys have been destroyed by a wipe. So if your friend trusts AES-256, then he can trust that the data is gone after a wipe.

That is good to know, I didn't realize the disk was encrypted.
–
BobJun 5 '12 at 19:17

@Bob- It only is encrypted if you turn on that option. The ultimate solution would be to, of course wipe the drive using the option to do so, then turn on the full disk encryption, and simply provide the key when the device is sold. This would mean the entire disk is encrypted, which means everything on it would be random data, including the data that was already there. Of course the fact the storage was flash based means, this process is sort of useless, since a normal person wouldn't be able to recover the data from said storage.
–
RamhoundAug 10 '12 at 12:03

After jailbreaking your iPad 2 and installing Cydia, you can install an OpenSSH server (included in the Cydia/Telesphoreo repository) on your iPad.

The OpenSSH server should start upon installation. Get your iPad's IP address by going to the Settings app, pressing "Wi-Fi", clicking the blue arrow by the network you're currently connected to, and looking at "IP Address".

You'll need a Unix-like terminal next. (On Windows, you can use PuTTY.)

Run this command in your terminal:

ssh root@your-ipads-ip-address

You'll be prompted for a password. By default, it is alpine. Type that in and press Enter.

You should have authenticated. This command will change your current working directory to the mounted "user partition", /var:

cd /var

Now you can begin wiping the free space with dd:

dd if=/dev/zero of=nothing.dat

This process may take a long time, and dd does not have a progress bar. Make sure your iPad is plugged in while this wipe takes place.

dd will output a brief transfer statistic upon completion (or error, but there shouldn't be any errors). Now, your free space is completely used up by a file called nothing.dat. Remove it to reclaim the free space:

rm nothing.dat

There you have it. The free space of the user partition has now been wiped with zeros!

Alternate (non-free) method:

After jailbreaking your iPad 2 and installing Cydia, you can use Cydia to purchase ($2.99) iWipe from the Cydia/Telesphoreo repository. Here is the description for iWipe (retrieved 05 June 2012 for version 1.0-1):

Want to make sure a deleted confidential email or embarrassing photo is purged forever from your iPhone? Simply deleting a file doesn't guarantee it's gone for good, and doing a restore only quick-formats the iPhone. Protect your deleted data from being recovered by hacking tools and prying eyes, or in the event your iPhone is stolen.

iWipe is a simple utility for zeroing out the free space on your iPhone. The tool does not delete any live files, but uses the same method that Mac OS X uses to zero free space: it creates a large temporary file, which writes zeroes over the free space where deleted files can still reside. The entire iPhone user partition is cleansed, forever purging deleted photos, email, voicemail, and other deleted files.

This helpful utility can be run periodically to effortlessly clear out old data and ensure it is beyond recovery. Because it doesn't erase your content or settings, you won't need to recovery any backups or risk losing data. Actual erase time varies depending on the amount of free space on the device. You're still able to lock or receive phone calls while iWipe is running.